Hydrochloric Acid → 3-[3-Fluoro-4-(4-phenoxybenzyloxy)phenyl]propanoic acid

HRID 1678590Notes

Reaction equation

HRID 1678590 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:23][CH2:24][C:25]([O:27]CC)=[O:26])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1.[OH-].[Na+].Cl>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH2:23][CH2:24][C:25]([OH:27])=[O:26])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23136285HCID 23136285, compound

Product 1

HCID 231364383-[3-Fluoro-4-(4-phenoxybenzyloxy)phenyl]propanoic acidYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 3-[3-fluoro-4-(4-phenoxybenzyloxy)phenyl]propanoate (0.16 g, 0.41 mmol) in ethanol (3 mL) was added a 2 N aqueous sodium hydroxide solution (3 mL), and the mixture was stirred at room temperature for 2 hours. To the reaction solution was added 2 N hydrochloric acid (3 mL), and the mixture was extracted with ethyl acetate. The extract was washed with water, and then concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound (0.14 g, yield 94%) as white powders.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-3d5a5cc67aa24146b2067724a502a701
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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